A PRACTICAL NEW ASYMMETRIC-SYNTHESIS OF (2S,3S)-3-HYDROXYLEUCINE AND (2R,3R)-3-HYDROXYLEUCINE

Authors
HALE KJ MANAVIAZAR S DELISSER VM
Citation
Kj. Hale et al., A PRACTICAL NEW ASYMMETRIC-SYNTHESIS OF (2S,3S)-3-HYDROXYLEUCINE AND (2R,3R)-3-HYDROXYLEUCINE, Tetrahedron, 50(30), 1994, pp. 9181-9188
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
30
Year of publication
1994
Pages
9181 - 9188
Database
ISI
SICI code
0040-4020(1994)50:30<9181:APNAO(>2.0.ZU;2-L
Abstract
A convenient new asymmetric synthesis of both enantiomers of erythro-3 -hydroxyleucine is described. The key steps involve Sharpless asymmetr ic dihydroxylation (AD) of a,a-unsaturated ester 3, cyclic sulphate fo rmation from the resulting diol, S(N)2 reaction with sodium azide, dee sterification with aqueous sodium hydroxide, and hydrogenolysis. Utili sing this route, (2S,3S)-(+)3-hydroxyleucine (1) was obtained in 97% e e and 67% overall yield; the (2R,3R)-(-)-enantiomer was isolated in 92 % ee and 57% overall yield.